


First Time for Everything

by rcumm20



Series: Slutty Jim [4]
Category: The Office (US)
Genre: Anal Sex, Bottom Jim, Gay Sex, M/M, Office Sex, Oral Sex, Smut, Top Roy, Warehouse sex
Language: English
Status: Completed
Published: 2021-02-17
Updated: 2021-02-17
Packaged: 2021-03-12 17:02:19
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,159
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29512914
Author URL: https://archiveofourown.org/users/rcumm20/pseuds/rcumm20
Summary: Jim runs into another strange situation with a coworker, but this time things go in a different way than expected.
Relationships: Jim Halpert/Roy Anderson
Series: Slutty Jim [4]
Series URL: https://archiveofourown.org/series/2140644
Kudos: 11





	First Time for Everything

Michael handed Jim a stack of papers. “As my new co-manager, you gotta get Roy to sign those by the end of the day today,” he said, too lazy to go get the signatures himself.

“Got it. I’ll leave them with Pam when I’m done,” Jim replied.

“Perfecto.”

Jim winked at his wife as he walked past her desk on his way to the stairs. He made his way to the warehouse and waved to Daryl and a couple of the other workers as he walked towards Roy’s office. He knocked on the door and Roy answered, “come on in Michael.”

“Oh, Michael sent me down instead,” Jim responded as he opened the door, but he froze as he saw Roy. The buff warehouse worker was sitting on his chair, buck naked.

Roy went red and scrambled for his clothing to cover up his bottom half. “Oh! Umm... Close the door! Jim, I— I wasn’t expecting you.”

Jim closed the door. “You were expecting Michael apparently.” Jim knew exactly what was going on here.

“Oh, no,” Roy said, immediately trying to defend his ‘manhood.’ 

“Oh I was just... I was—,” Jim interrupted him before he could finish his sentence.

“It’s fine Roy, I understand. How do you think I got my promotion?” Jim said with a smirk.

“I wasn’t expecting that,” Roy paused.

“Still, I don’t think Michael’s gonna give you anything for free. I can put in a good word for you, if you want?” Roy nodded his head in response. “You know what you gotta do if you want that good word though, don’t you?” Roy nodded again.

“But, I have a request.” Roy interjected. “I believe you owe me one.” 

“Owe you what?” Jim inquired, not sure where this was going.

Roy stood up, dropping his lower coverage. “You stole my fiancé, so I want to steal something of yours,” he stepped towards Jim and pulled him close. He pinched Jim’s right cheek and winked at him.

“Oh...” Jim got his message. He thought to himself that it was only fair, and it wasn’t the worst price to pay. He also knew that it would happen eventually, so why not get it over with. “Deal,” Jim answered, slightly nervous to be penetrated by such a big man on his first go around.

Roy pulled down Jim’s already unbuckled pants and began stroking his friend’s not-so-little friend while on his knees. He observed that though his own penis wasn’t as long as Jim’s, it certainly exceded his girth, and Jim noticed it too. Soon, Jim’s whole length was down Roy’s throat. Roy barely had a gag reflex and Jim noticed that too. Roy was able to slide the long cock down his throat with ease, and he did it quicker than most too. Jim’s nerves were calmed by this experience.

Eventually Roy released Jim’s dick from his mouth and opened the bottom desk drawer. He pulled out condoms and lube and set them on his desk. He then stood up to meet Jim’s eye level and asked, “You ready for this?” And Jim responded with a now confident, ‘Yes.’

Roy bent Jim over and his arms rested on the desk, and Roy went around back. He returned to his knees, his eyes now level with Jim’s tight, virgin hole. Roy spread Jim’s pale, hairy cheeks and went in on him. He entered his tongue into his partners hole and Jim gasped, surprised by the new feeling.

“You like it, don’t you?” Roy asked in between rimming.

“Oh yeah. Yeah, so far,” Jim responded near out of breath despite the fact that he wasn’t moving.

Roy continued on.

With Jim’s ass slobbered up and wet, Roy now tested his sensitivity with one finger, and then another, and then another. Jim inhaled sharply with every re-entrance. Roy checked on him frequently, making sure this was as pleasurable as possible, and every time Jim replied with a “keep going,” or simply a moan.

With Jim now fully prepared, Roy slid on a condom and applied lube to himself and his partner. After confirming Jim’s readiness, Roy aligned his dick with Jim’s hole. Slowly, he entered Jim, and neither of them could help but moan. Jim embraced the foreign feeling, trying his hardest not to move too much. His hole spread wider than in preparation, Roy’s cock being too girthy to properly prepare for.

Jim’s moans reached a peak as Roy’s hips clapped against Jim’s cheeks. Roy responded in harmony with grunts of his own as he began to rock back and forth into Jim. Jim was starting to feel more pleasured with every thrust. His hole had gotten used to the wide state, and was accepting as Roy entered in each time. Soon, Jim felt confident in his abilities as a bottom.

Roy pulled out, leaving Jim’s hole feeling very empty, and Jim turned around. “Lay down. I want to have some control.” Roy was happy to oblige.

With Roy faced up on the ground, Jim straddled the larger, more muscled man. Jim took Roy’s cock and sat down on it, taking even more pleasure in the now familiar feeling. With some time for adjustment, he was soon rocking back and forth, riding Roy like a true cowboy. He put his hands on either of Roys pecs to act as stabilization as his lower half continued working.

Roy found it difficult not to squirm with pleasure and Jim continued to ride him. He moaned louder at this time, now harder to resist as he sat still. To increase participation and pleasure, Roy helped Jim out by jerking him off. From his awkward position, it was slower than usual, but that didn’t seem to bother Jim because his moans only lengthened. 

Jim, being more inexperienced with being a bottom, was brought to his climax first. Jim had never felt this type of orgasm. It was a whole different experience. His cum splattered onto Roy’s chest and up to his face, and Roy could taste some from his cheek. Still riding, determined to guide Roy to his own orgasm, Jim licked up his semen and brought it to Roy’s mouth where they kissed, blending their fluids. 

Soon enough, Roy felt his climax creeping up on him. He quickly slid out of Jim, again leaving his hole feeling empty, and tore off his condom. He kneeled in front of Jim, this time having Jim lower than him. Jim had his mouth open, waiting for a shower of Roy’s sweet, sweet cum. He pet Roy’s hairy legs as the man jerked his own cock, beginning to moan. It wasn’t long before their lips were locked once more, their fluids mixing again.

Jim was incredibly satisfied and surprised by that experience. Roy was not surprised at all, but most definitely satisfied. The two of them kissed once again after they had cleaned up, almost as a thank you, and Jim returned upstairs with the paper.

**Author's Note:**

> Thanks for reading! This will most likely be the last in the Slutty Jim series for the time being, but there will be more eventually (look out for Pete!). I’m so grateful for all the support on these works!


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